Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
  • A61L9/00—Disinfection, sterilisation or deodorisation of air
  • A61L9/01—Deodorant compositions
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/35—Ketones, e.g. benzophenone
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
  • A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
  • A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
  • A61L2/18—Liquid substances or solutions comprising solids or dissolved gases
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
  • A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
  • A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
  • A61L2/22—Phase substances, e.g. smokes, aerosols or sprayed or atomised substances
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
  • A61L9/00—Disinfection, sterilisation or deodorisation of air
  • A61L9/14—Disinfection, sterilisation or deodorisation of air using sprayed or atomised substances including air-liquid contact processes
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q15/00—Anti-perspirants or body deodorants
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
  • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
  • C07C49/207—Unsaturated compounds containing keto groups bound to acyclic carbon atoms with only carbon-to-carbon triple bonds as unsaturation
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
  • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
  • C07C49/213—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
  • C07C49/217—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the aromatic rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
  • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
  • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
  • C07D307/40—Radicals substituted by oxygen atoms
  • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
  • A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
  • A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
  • A61L2/23—Solid substances, e.g. granules, powders, blocks, tablets
  • A61L2/232—Solid substances, e.g. granules, powders, blocks, tablets layered or coated
• • A61L2103/75—
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
  • A61L2209/00—Aspects relating to disinfection, sterilisation or deodorisation of air
  • A61L2209/20—Method-related aspects
  • A61L2209/21—Use of chemical compounds for treating air or the like

Definitions

• the present application relates to new deodorant compositions containing at least one compound of the acetylenic ketone family and deodorizing products containing them.
• deodorant composition refers to a composition whose deodorant effect is related to the properties of physical destruction of malodorous molecules by acetylenic ketones and not any masking of the bad smell.
• the subject of the invention is primarily a deodorant composition characterized in that it comprises at least one compound of the family of acetylenic ketones having the general formula 1 R- (CO) ⁇ -C ⁇ C- (A) - ( C ⁇ C) m - (CO) n - R 1 (1) in which
• R and R 1 can represent, independently or simultaneously, a radical chosen from an alkyl chain comprising from 1 to 9, preferably from 3 to 7 carbon atoms, linear or branched, substituted or unsubstituted, or a cycloalkane comprising from 3 to 8, preferably from 5 to 6 carbon atoms, substituted or unsubstituted; or o a furanic ring, saturated or unsaturated, substituted or unsubstituted; or o a pyranic ring, saturated or unsaturated, substituted or unsubstituted; or o an aromatic ring comprising from 6 to 8 carbon atoms, substituted or unsubstituted; or else a hydrogen atom.
• A represents a group chosen from - (CHa) x with x representing an integer of value 0 to 6, preferably from 0 to 4, (-CO) ⁇ with I representing an integer of value 0 or 1, or else a sequence - (CH 2 ) y -O- (CH 2 ) z- with y and z representing, simultaneously or independently, an integer of value 0 to 6, preferably 0 to 4, it being understood that x + y does not exceed the value 6 ;
• alkyl chain comprising from 1 to 9 carbon atoms, a methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl or nonyl radical, linear or branched, substituted or unsubstituted, in particular by a or groups (s) oxo, without however that the total of carbon atoms in the molecule does not exceed 18, preferably 16.
• a cycloalkane comprising from 3 to 8 carbon atoms is understood to mean a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopropylmethyl or cyclobutylmethyl radical.
• an aromatic ring comprising from 6 to
• the radicals R and R 1 may be simultaneously or independently substituted by one or more radicals chosen from methyl, ethyl, propyl and butyl radicals or a 2-oxopropyl radical.
• R 1 and R 1 may preferably be an acetonyl, pentyl, hexyl, heptyl, cyclopropyl, cyclopentyl, cyclohexyl, furyl or phenyl, anisyl, dimethoxyphenyl, tolyl radical and R 1 may be a hydrogen atom.
• the compound of formula 1 may be in the composition in an amount of between 0.01% and 40%, preferably between 0.1% and 15%, even more preferably between 1% and 10% by total weight. of the composition.
• the composition may comprise one or more compounds corresponding to formula 1. According to the invention, it is preferable to use in the compositions at least one of the compounds chosen from:
• 1,4-diphenyl-2-butyn-1 4-dione / 1 - (p-tolyl) -2-butyn-1-one; 4,7-undecadiyn-6-one / 1- (p-tolyl) -2-butyn-1-one;
• the compound of formula 1 may be in the composition present in an amount of between 0.1% and 40%, preferably between 0.1% and 10%, by total weight of the composition.
• the compounds of formula 1 are known for their high reactivity with thiols and amines.
• the deodorizing composition may further comprise at least one aldehyde chosen from aliphatic acyclic and non-terpene aldehydes, non-terpenic alicyclic aldehydes, terpene aldehydes, aliphatic aldehyde aldehydes substituted by an aromatic group, aldehydes.
• the composition may comprise a mixture of two or more aldehydes.
• the deodorizing composition may also comprise a mixture of at least one first aldehyde (aldehyde of class A) chosen from aliphatic acyclic and non-terpene aldehydes, non-terpenic alicyclic aldehydes, terpene aldehydes, aliphatic aldehydes substituted with an aromatic group and bifunctional aldehydes and at least one second aldehyde (aldehyde of class B) selected from aldehydes having a non-aromatic unsaturation carried by the alpha carbon of the aldehyde function, aldehydes having an alpha unsaturation of the aldehyde function conjugated with an aromatic ring and aldehydes whose function is carried by an aromatic ring.
• aldehyde of class A chosen from aliphatic acyclic and non-terpene aldehydes, non-terpenic alicyclic aldehydes, terpene aldehydes
• the composition may comprise a mixture of at least one first and at least one second aldehyde.
• first aldehyde may be a mixture of two or more class A aldehydes and the second aldehyde may be a mixture of two or more aldehydes selected from those of class B.
• the class A or B aldehydes can be chosen from natural or synthetic aldehydes, particularly from those classified as non-dangerous for the environment according to the European directive "Dangerous substances", authorized in food (No. FEMA) and in perfumery by IFRA.
• the acyclic and non-terpene aliphatic aldehyde of class A may be chosen from
• non-terpene alicyclic aldehyde of class A may be chosen from
• the non-terpenic alicyclic aldehyde aldehyde (AlNNT) of class A may be selected from 0 - 8,8-dimethyl-2,3,4,5,6,7-hexahydro-1H-naphthalene-2-carboxaldehyde (ALDEHYDE 111 TM );
• Terpene aldehyde (Terp) of class A may be chosen from 0 - citronellal;
• the terpene aldehyde may be chosen from
• the aliphatic aldehyde of class A substituted with an aromatic group may be chosen from
• the aliphatic aldehyde substituted with an aromatic group may be chosen from - 2-methyl-3- (p-isopropylphenyl) propanal;
• bifunctional aldehyde means aldehydes which also have another function, for example an ether-oxide or alcohol function.
• the bifunctional aldehyde may be according to the invention chosen from alkoxyacetaldehydes;
• alkoxy aldehydes as for example - 3 and 4- (4-hydroxy-4-methylpentyl) -3-cyclohexen-1-carboxaldehyde
• the bifunctional aldehyde can be any organic compound having 7-hydroxy-3,7-dimethyloctanal (hydroxycitronellal).
• the bifunctional aldehyde can be any organic compound having 7-hydroxy-3,7-dimethyloctanal (hydroxycitronellal).
• the bifunctional aldehyde can be any organic compound having 7-hydroxy-3,7-dimethyloctanal (hydroxycitronellal).
• the bifunctional aldehyde can be any organic compound having 7-hydroxy-3,7-dimethyloctanal (hydroxycitronellal).
• the aldehyde which has a non-aromatic unsaturation (class B) carried by the carbon in the alpha position of the aldehyde function can be chosen from
• citral neral and geranial
• substituted or unsubstituted furyl-2-carboxaldehydes preferably those which are unsubstituted or substituted with at least one methyl;
• the aldehyde which has a non-aromatic unsaturation (class B) carried by the carbon in the alpha position of the aldehyde function may be
• aldehyde (class B) which has an ethylenic unsaturation in alpha, conjugated with an aromatic ring can be chosen from
• the aldehyde which has an ethylenic unsaturation in alpha, conjugated with an aromatic ring can be
• the aldehyde carried by an aromatic ring may be selected from vanillin;
• an aromatic ring itself optionally substituted elsewhere, may be chosen from
• the first aldehyde may be chosen preferably from aliphatic acyclic and non-terpenic aldehydes, non-terpenic alicyclic aldehydes, terpene aldehydes and aldehydes.
• the aldehyde may be preferably selected from aldehydes which have a non-aromatic unsaturation carried by the alpha carbon.
• the first aldehyde may be selected from aliphatic or acyclic and non-terpene aldehydes and the second from terpene aldehydes having alpha carbon unsaturation above.
• Particularly interesting pairs of aldehydes can be chosen especially from the following pairs, without any limitation:
• the composition may comprise the aldehyde in an amount of between 0.5% and 50% of the composition, preferably in an amount of between 1% and 20% of the composition.
• the composition may comprise aldehydes of classes A and B in relative proportions with respect to each other in proportions of 80/20 to 20/80, especially in proportions of 50/50 and in a total amount of aldehydes of between 1% and 90% of the composition, preferably in an amount of between 10% and 30% of the composition.
• the deodorizing compositions according to the invention in addition to their remarkable deodorizing properties, also have in themselves odoriferous properties possibly capable of replacing odors with their own odor.
• the deodorizing compositions may further comprise a masking agent.
• These compositions may therefore comprise at least one odoriferous agent such as those usually used in perfumery, such as alcohols, essential oils, phenolic substances and esters.
• compositions according to the invention may also contain specific substances, for example bactericidal agents.
• deodorizing compositions are advantageously formulated according to the usual techniques. This is why the present application also relates to deodorant products characterized in that they contain the compositions described above.
• These products may be in the form of aerosol sprays, impregnated solid carriers, liquids, creams, powders, etc. They can be made according to methods known to those skilled in the art.
• the subject of the invention is also the use of a compound of the family of acetylenic ketones corresponding to formula 1 in a deodorizing composition, particularly in deodorant compositions comprising at least one aldehyde selected from acyclic and non-terpene aliphatic aldehydes, non-terpenic alicyclic aldehydes, terpene aldehydes, aromatic-substituted aliphatic aldehydes, bifunctional aldehydes, aldehydes having a non-aromatic carbon-borne unsaturation; alpha of the aldehyde function, the aldehydes having an alpha unsaturation of the aldehyde function conjugated with an aromatic ring and the aldehydes whose function is carried by an aromatic ring, and even more preferably in a deodorizing composition comprising a mixture of at least a first aldehyde (class A aldehyde) selected from acyclic and non-terpene
• Figure 1 illustrates the degradation of butylamine under the effect of acetylenic ketones according to the invention.
• FIG. 2 illustrates the degradation of butylamine under the effect of a known neutralizing agent to which an acetylenic ketone according to the invention is added.
• 2-methyl-5-decyn-4-one and 9-methyl-5-decyn-4-one and 1-pheryl-1-pentyn-3-one are prepared (the latter a single isomer, a single site of the starting 1-phenyl-1-pentyne that can be oxidized).
• HM Protocol The olfactory test is performed with an expert panel of 25 people.
• the acetylenic ketones to be tested are prepared at a concentration of 1 mol / L in dipropylen glycol.
• the malodorous reference solution is also prepared at a concentration of 1 mol / L.
• a first pillbox contains 1 g of the malodorous reference solution.
• the bad smell released by the first pillbox is assigned the reference value 10 (malodorous reference solution).
• the results are then converted to the percentage of remaining bad odor.
• This test aims to show the potentiating effect of acetylenic ketones on a deodorant already known, the neutral 1.
• a bad kitchen smell is prepared by mixing the following different compounds:
• the panel of testers then evaluates the odor in each of the speakers, in the order defined by a Latin square and in comparison with the reference chamber containing the bad odor alone.
• a bad smell of tobacco is prepared from ashes and cigarette butts. 20 g of this odor are deposited in an olfaction cabin of 3 m 3 .
• Cloth napkins are left in the enclosure and left 24 hours to soak up the smell of tobacco.
• the panel then evaluates the amount of tobacco smell on the towels compared to the towels that have not been treated with the bad smell.
• Neutral 2 The effectiveness of Neutral 2 is improved by adding at least one acetylenic ketone.
• a bad toilet smell is prepared by mixing the following different compounds:
• 20 ⁇ l_ of this bad smell are deposited in the water of a toilet bowl in the cabin.
• 20 ⁇ l_ of bad smell are deposited as well as 20 ⁇ ! _ Of a neutral 3 active against the bad smell of toilets.
• an acetylenic ketone (99/1) is additionally added to neutral 3.
• the amount of toilet odor in each cabin is then evaluated by the panel of testers.
• T neutral 3 and 5-decyn-4-one of formula C 4 Hg-CsC-CO-C 3 H 7 ;
• Quantity compound (vol./vol.)
• OdT + T 23 The effectiveness of neutral 3 is improved by adding at least one acetylenic ketone.
• Parallel tests help to report the reactivity of acetylenic ketones. They are made by reacting mole to mole an acetylenic ketone with a substance responsible for a bad smell. The reaction is carried out at room temperature in THF.
• a substrate, piperidine, is used to verify this reactivity.
• the reaction is carried out at ambient temperature in THF).
• the peak areas are used to determine the amount of residual butylamine (bad smell).
• the analyzes are made chromatographies every 25 min. to establish kinetics.
• acetylenic ketones When used alone in 1/10 ratio (acetylenic ketone / butylamine), acetylenic ketones reduce the amount of butylamine by 4 to 8% in less than 3 hours.
• Aldehydes can also be formulated as acetals to reduce the intrinsic odor of the neutralizer and increase the duration of action. It is known that an acetal hydrolyses in acidic medium by releasing the corresponding aldehyde.
• some weakly odorous acetals that can be used in a surface deodorant: propionaldehyde DEA, phenylacetaldehyde-methanol acetal, citral diethylacetal, hydroxycitronnellal dimethylacetal, benzaldehyde diethylacetal.
• Surface deodorant formula :

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• Health & Medical Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• General Health & Medical Sciences (AREA)
• Public Health (AREA)
• Veterinary Medicine (AREA)
• Epidemiology (AREA)
• Chemical Kinetics & Catalysis (AREA)
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• Birds (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Gas Separation By Absorption (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Cosmetics (AREA)
• Fats And Perfumes (AREA)
• Disinfection, Sterilisation Or Deodorisation Of Air (AREA)

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• 2009
  • 2009-06-18 EP EP09007987A patent/EP2272491A1/de not_active Withdrawn
• 2010
  • 2010-06-17 WO PCT/FR2010/000448 patent/WO2010146258A2/fr not_active Ceased
  • 2010-06-17 US US13/379,278 patent/US9265852B2/en active Active
  • 2010-06-17 EP EP10734772.6A patent/EP2442783B1/de active Active

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